4-(6-Quinolyl-oxymeth-yl)benzonitrile.

The title compound, C(17)H(12)N(2)O, was synthesized by an ether synthesis from quinolin-6-ol and 4-(bromo-meth-yl)benzonitrile. The phenyl ring of the benzonitrile group makes a dihedral angle of 47.52 (6)° with the plane of the quinoline fragment. The crystal structure is stabilized by inter-molecular C-H⋯π inter-actions between a benzene H atom of the benzonitrile group and the benzene ring of the quinoline fragment. In addition, the crystal structure also exhibits a weak inter-molecular C-H⋯N hydrogen bond.

Related literature

For general background to nitrile compounds, see: Jin et al. (1994 ▶); Brewis et al. (2003 ▶). For related structures, see: Fu & Zhao (2007 ▶); Zhao (2008 ▶).

Experimental

Crystal data

C17H12N2O

M = 260.29

Monoclinic,

a = 9.466 (2) Å

b = 13.078 (3) Å

c = 10.857 (2) Å

β = 90.81 (3)°

V = 1343.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.26 × 0.24 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.976, T max = 0.981

12007 measured reflections

2622 independent reflections

1956 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.120

S = 1.06

2622 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016560/lx2099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016560/lx2099Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H12N2O	F(000) = 544
Mr = 260.29	Dx = 1.286 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10916 reflections
a = 9.466 (2) Å	θ = 6.2–55.5°
b = 13.078 (3) Å	µ = 0.08 mm−1
c = 10.857 (2) Å	T = 293 K
β = 90.81 (3)°	Prism, colourless
V = 1343.9 (5) Å3	0.30 × 0.26 × 0.24 mm
Z = 4

Rigaku SCXmini diffractometer	2622 independent reflections
Radiation source: fine-focus sealed tube	1956 reflections with I > 2σ(I)
graphite	Rint = 0.054
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
Tmin = 0.976, Tmax = 0.981	l = −13→13
12007 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.050P)2 + 0.1913P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2622 reflections	Δρmax = 0.14 e Å−3
182 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (4)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.48772 (13)	0.46617 (8)	0.29375 (10)	0.0598 (4)
N1	0.40388 (17)	0.05815 (11)	0.18437 (15)	0.0620 (4)
N2	0.7214 (2)	0.99565 (14)	0.44097 (18)	0.0841 (6)
C1	0.46122 (17)	0.36816 (12)	0.25614 (16)	0.0484 (4)
C2	0.49253 (18)	0.29346 (13)	0.34606 (16)	0.0538 (5)
H2	0.5251	0.3134	0.4236	0.065*
C3	0.47550 (19)	0.19262 (13)	0.32018 (16)	0.0547 (5)
H3	0.4984	0.1441	0.3798	0.066*
C4	0.42364 (17)	0.16054 (12)	0.20416 (16)	0.0478 (4)
C5	0.3504 (2)	0.03171 (15)	0.07708 (19)	0.0701 (6)
H5	0.3356	−0.0376	0.0624	0.084*
C6	0.3139 (2)	0.10024 (15)	−0.01687 (19)	0.0691 (6)
H6	0.2764	0.0765	−0.0912	0.083*
C7	0.33370 (19)	0.20151 (13)	0.00168 (16)	0.0570 (5)
H7	0.3103	0.2482	−0.0599	0.068*
C8	0.39011 (16)	0.23550 (12)	0.11523 (15)	0.0451 (4)
C9	0.40997 (17)	0.34014 (12)	0.14319 (15)	0.0474 (4)
H9	0.3881	0.3898	0.0846	0.057*
C10	0.45964 (19)	0.54615 (12)	0.20742 (16)	0.0526 (4)
H10A	0.3588	0.5517	0.1918	0.063*
H10B	0.5056	0.5316	0.1301	0.063*
C11	0.51542 (17)	0.64433 (12)	0.26109 (15)	0.0478 (4)
C12	0.43628 (18)	0.73295 (12)	0.25445 (17)	0.0531 (5)
H12	0.3466	0.7310	0.2185	0.064*
C13	0.48752 (18)	0.82412 (13)	0.30002 (17)	0.0552 (5)
H13	0.4330	0.8831	0.2948	0.066*
C14	0.62108 (18)	0.82714 (12)	0.35366 (15)	0.0494 (4)
C15	0.70261 (19)	0.73897 (13)	0.35993 (17)	0.0576 (5)
H15	0.7927	0.7410	0.3951	0.069*
C16	0.64942 (19)	0.64883 (13)	0.31393 (17)	0.0574 (5)
H16	0.7042	0.5899	0.3183	0.069*
C17	0.6764 (2)	0.92132 (15)	0.40205 (17)	0.0607 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0811 (9)	0.0411 (7)	0.0567 (8)	−0.0085 (6)	−0.0115 (6)	0.0033 (5)
N1	0.0743 (11)	0.0411 (9)	0.0705 (11)	0.0007 (7)	0.0028 (8)	0.0007 (7)
N2	0.0966 (13)	0.0606 (11)	0.0946 (13)	−0.0189 (10)	−0.0163 (10)	−0.0113 (10)
C1	0.0489 (9)	0.0409 (9)	0.0551 (10)	−0.0042 (7)	−0.0015 (8)	0.0030 (8)
C2	0.0596 (11)	0.0524 (11)	0.0494 (10)	−0.0030 (8)	−0.0063 (8)	0.0048 (8)
C3	0.0610 (11)	0.0479 (11)	0.0553 (11)	0.0019 (8)	−0.0030 (8)	0.0128 (8)
C4	0.0455 (9)	0.0412 (10)	0.0569 (11)	0.0011 (7)	0.0043 (8)	0.0037 (8)
C5	0.0847 (15)	0.0449 (11)	0.0808 (15)	−0.0049 (9)	0.0041 (11)	−0.0085 (10)
C6	0.0842 (14)	0.0584 (12)	0.0646 (12)	−0.0103 (10)	−0.0065 (10)	−0.0105 (10)
C7	0.0635 (12)	0.0526 (11)	0.0546 (11)	−0.0049 (8)	−0.0053 (9)	0.0016 (8)
C8	0.0396 (9)	0.0439 (9)	0.0516 (10)	−0.0019 (7)	0.0007 (7)	0.0025 (7)
C9	0.0502 (10)	0.0433 (9)	0.0485 (10)	−0.0011 (7)	−0.0052 (7)	0.0089 (7)
C10	0.0589 (11)	0.0427 (10)	0.0562 (11)	−0.0010 (8)	−0.0035 (8)	0.0040 (8)
C11	0.0489 (10)	0.0431 (10)	0.0514 (10)	−0.0033 (7)	0.0032 (7)	0.0030 (7)
C12	0.0439 (10)	0.0472 (10)	0.0681 (12)	−0.0011 (7)	−0.0023 (8)	0.0004 (8)
C13	0.0534 (11)	0.0418 (10)	0.0706 (12)	0.0031 (8)	0.0033 (9)	0.0025 (8)
C14	0.0543 (11)	0.0434 (9)	0.0506 (10)	−0.0084 (7)	0.0036 (8)	0.0015 (7)
C15	0.0499 (10)	0.0553 (11)	0.0673 (12)	−0.0016 (8)	−0.0093 (9)	0.0009 (9)
C16	0.0559 (11)	0.0442 (10)	0.0718 (12)	0.0069 (8)	−0.0075 (9)	0.0004 (8)
C17	0.0664 (12)	0.0532 (11)	0.0626 (12)	−0.0073 (9)	−0.0030 (9)	0.0002 (9)

O1—C1	1.3674 (19)	C7—H7	0.9300
O1—C10	1.4269 (19)	C8—C9	1.414 (2)
N1—C5	1.310 (2)	C9—H9	0.9300
N1—C4	1.369 (2)	C10—C11	1.503 (2)
N2—C17	1.140 (2)	C10—H10A	0.9700
C1—C9	1.363 (2)	C10—H10B	0.9700
C1—C2	1.410 (2)	C11—C12	1.381 (2)
C2—C3	1.358 (2)	C11—C16	1.386 (2)
C2—H2	0.9300	C12—C13	1.377 (2)
C3—C4	1.409 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.385 (2)
C4—C8	1.409 (2)	C13—H13	0.9300
C5—C6	1.398 (3)	C14—C15	1.389 (2)
C5—H5	0.9300	C14—C17	1.435 (2)
C6—C7	1.352 (3)	C15—C16	1.373 (2)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.408 (2)	C16—H16	0.9300
C1—O1—C10	117.34 (12)	C1—C9—H9	120.1
C5—N1—C4	116.62 (16)	C8—C9—H9	120.1
C9—C1—O1	125.61 (15)	O1—C10—C11	108.09 (13)
C9—C1—C2	120.38 (15)	O1—C10—H10A	110.1
O1—C1—C2	114.01 (14)	C11—C10—H10A	110.1
C3—C2—C1	120.44 (16)	O1—C10—H10B	110.1
C3—C2—H2	119.8	C11—C10—H10B	110.1
C1—C2—H2	119.8	H10A—C10—H10B	108.4
C2—C3—C4	120.86 (16)	C12—C11—C16	118.59 (15)
C2—C3—H3	119.6	C12—C11—C10	120.62 (15)
C4—C3—H3	119.6	C16—C11—C10	120.74 (15)
N1—C4—C8	122.97 (16)	C13—C12—C11	121.32 (16)
N1—C4—C3	118.47 (15)	C13—C12—H12	119.3
C8—C4—C3	118.53 (15)	C11—C12—H12	119.3
N1—C5—C6	124.62 (18)	C12—C13—C14	119.39 (16)
N1—C5—H5	117.7	C12—C13—H13	120.3
C6—C5—H5	117.7	C14—C13—H13	120.3
C7—C6—C5	119.14 (18)	C13—C14—C15	120.02 (15)
C7—C6—H6	120.4	C13—C14—C17	120.32 (16)
C5—C6—H6	120.4	C15—C14—C17	119.67 (16)
C6—C7—C8	119.31 (17)	C16—C15—C14	119.63 (16)
C6—C7—H7	120.3	C16—C15—H15	120.2
C8—C7—H7	120.3	C14—C15—H15	120.2
C7—C8—C4	117.33 (15)	C15—C16—C11	121.04 (16)
C7—C8—C9	122.75 (15)	C15—C16—H16	119.5
C4—C8—C9	119.89 (15)	C11—C16—H16	119.5
C1—C9—C8	119.88 (15)	N2—C17—C14	179.4 (2)
C10—O1—C1—C9	−0.1 (2)	O1—C1—C9—C8	178.66 (15)
C10—O1—C1—C2	179.55 (14)	C2—C1—C9—C8	−1.0 (2)
C9—C1—C2—C3	1.7 (3)	C7—C8—C9—C1	178.09 (16)
O1—C1—C2—C3	−177.98 (16)	C4—C8—C9—C1	−0.1 (2)
C1—C2—C3—C4	−1.3 (3)	C1—O1—C10—C11	−171.97 (14)
C5—N1—C4—C8	−0.4 (3)	O1—C10—C11—C12	−135.85 (16)
C5—N1—C4—C3	177.42 (17)	O1—C10—C11—C16	46.7 (2)
C2—C3—C4—N1	−177.77 (16)	C16—C11—C12—C13	−0.6 (3)
C2—C3—C4—C8	0.2 (3)	C10—C11—C12—C13	−178.12 (16)
C4—N1—C5—C6	0.5 (3)	C11—C12—C13—C14	0.0 (3)
N1—C5—C6—C7	−0.1 (3)	C12—C13—C14—C15	0.7 (3)
C5—C6—C7—C8	−0.2 (3)	C12—C13—C14—C17	−179.84 (16)
C6—C7—C8—C4	0.3 (2)	C13—C14—C15—C16	−0.7 (3)
C6—C7—C8—C9	−178.00 (17)	C17—C14—C15—C16	179.81 (17)
N1—C4—C8—C7	0.1 (2)	C14—C15—C16—C11	0.1 (3)
C3—C4—C8—C7	−177.76 (16)	C12—C11—C16—C15	0.6 (3)
N1—C4—C8—C9	178.39 (15)	C10—C11—C16—C15	178.10 (16)
C3—C4—C8—C9	0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cgi	0.93	2.83	3.613 (2)	142
C13—H13···N1ii	0.93	2.60	3.398 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cgi	0.93	2.83	3.613 (2)	142
C13—H13⋯N1ii	0.93	2.60	3.398 (2)	145

Symmetry codes: (i) ; (ii) . Cg is the centroid of the C1–C4/C8/C9 benzene ring.